When Should You Talk to an Employee About Their Time-Off Request?

In a perfect world, employee time off would never be an issue. Everybody would take the exact right number of days off at the exact right times in the exact right way.

Let’s pause for a minute to relish this perfect world of our imagination. . . . Why yes, I would love a large piece of your most delectable ice cream cake . . . . Free of charge? Why thank you!

OK, back to reality. Sometimes time-off requests cause issues. The challenge is deciding when the issues need special attention and when they do not. So, when is it time to talk to an employee about their time-off request? Here are a few things to consider.

Three Important Realities

Reality #1:Communication is key. What are your time-off policies? If they’re not clearly defined, you’re setting yourself up for failure. When emergencies or personal crises occur—and it’s particularly important that employers handle such situations carefully—the last thing you want to have to do is wing it.

Remember, clear policies lead to easier decisions.

For example, let’s say an employee suddenly has the trip of a lifetime come up with their whole family who hasn’t been together in years. Everyone is going, someone else is paying for it, and it’s an amazing three-week excursion. But they’re out of PTO time and didn’t know this opportunity would come up and really this will never happen again . . . A clear policy is the only defense a good-natured manager will have. Otherwise, that manager is likely to give in and approve the request regardless of the negative effects their absence may cause.

Reality #2: Respect is also key. The second reality is related to the first. When time-off policies don’t adequately cover a particular issue, always err on the side of respect. Always strive to be fair and compassionate with your employees, even—and perhaps especially—when you have to deliver bad news. Remember that time off is a benefit, so don’t kill the value of that benefit by how you allow or deny its usage.

Reality #3:Be aware of your time-off culture. This culture represents your employees’ expectations around time-off requests, and if you’re not careful, it will be confused with your actual policies. For example, if time-off requests are approved 99.9 percent of the time (assuming employees have available time off), your employees will conflate your time-off culture with your actual policies, and you will be in trouble when you decide to deny their request.

When it’s for sure, 100 percent time to discuss a time-off request

When the request goes against company policy.

This is pretty obvious, but it’s important enough to highlight. Generally speaking, it’s important to be consistent with company policies on time off. There will always be exceptions worth considering, but if you make exceptions the new rule, it will come back to bite you.

Just as the introduction of a new species can destroy an ecosystem, unwarranted exceptions to company policies can erode an organization’s culture.

So, when an employee makes a request that is against company policy, make sure to have a conversation with them about the situation. And then document the conversation. Whether you approve their request or not, your conversation—and its record—will help everybody understand they why behind each specific decision. Understanding these whys will inform future conversations and prevent possible conflicts.

When it may be time to discuss a time-off request

When you can demonstrate their absence will have a negative impact.

Obviously, you’d love to approve every time-off request, but what about those times when Employee X wants to leave during a crucial time in their work? In this situation, you may want to just deny their request without a second thought. But before you do that, you need to make sure you have a genuinely good reason for it.

It might be cumbersome (or annoying) to quantify the opportunity cost to the organization when an employee takes time off, but it’s probably necessary. Otherwise, it’ll just feel personal to the employee when you deny their request.

However, if you can link a clear business pain to an employee’s absence, you need to make sure they understand it as well. In many instances, they’ll be OK to move their time-off request to a better time.

If a time-off request is long enough that you’re not sure whether or not it qualifies as a leave of absence, you probably need to talk. There will, of course, be perfectly acceptable reasons for an extended absence, but you’ll want to make sure that’s the case with your employee. If not, there are a few things worth considering.

For starters, experts estimate that the perfect vacation length is somewhere between eight days and ten days. Also, frequent vacations (as opposed to using vacation days in one big chunk) are good for you.

On the other side of the equation, long absences can put a heavy workload on others in the organization, weighing them down and diminishing their ability to perform. When extended absences lead to poor performance, the previous point about business pain comes into play.

When a time-off request comes with too little notice.

This relates to what I mentioned earlier about respect. Sick days and legitimate emergencies are one thing, but impromptu trips and personal days can be unfair when they occur too frequently. Not only that, but taking off with very little notice can come across as unprofessional. Depending on the circumstances, this might cause more serious problems for the employee and their organization.

To be clear, there are times when an employee just needs to get away. Most people need a little spontaneity in their lives. The difficulty arises when the spontaneity becomes routine, leaving unfair burdens on others around them. When this is the case, it’s probably appropriate to talk with the employee and help them understand the effects of their sudden absences.

When time-off requests aren’t happening often enough. Sometimes employees need to be told to take time off. Only 23 percent of Americans take their full amount of available PTO, and an equal amount takes 25 percent or less of their allotted time. Simply put, this refusal to take take a break is bad for employees. So talk to them about time off, and make sure they know its benefits.

If push comes to shove, you might want to consider insisting employees take a vacation. (In case you’re wondering whether this is legal, the answer is more or less yes.) Now, force rarely leads to mutual respect, so you’ll want to avoid it all costs. Rather, work to persuade employees to take time off both through conversation and by building a culture where time off is encouraged. As difficult as it may be for some to accept, ultimately everybody will be better off when employees are taking time off appropriately.

Time off is a benefit—and one that should be benefitting both employees and employers alike. When it’s not, it’s probably time to talk to employees about their time-off requests.